1,3- and 1,2-unsaturated derivatives as valuable synthetic tools in organometallic syntheses

Current Organic Chemistry

Volumn 14, Issue 3, 2010, Pages 230-263

  Deagostino, Annamaria ^a   Prandi, Cristina ^a   Tabasso, Silvia ^a   Venturello, Paolo ^a  

^a UNIVERSITY OF TURIN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CARBONYL COMPOUNDS; CHEMICAL BONDS; IONIC LIQUIDS; ORGANOMETALLICS; REGIOSELECTIVITY; UNSATURATED COMPOUNDS;

ALLENES; COMPLEXES STRUCTURE; ELECTROPHILES; FUNCTIONALIZED; HECK COUPLING; ORGANOMETALLIC SYNTHESIS; PALLADIUM-CATALYZED REACTIONS; PROPARGYLIC ACETALS; SUZUKI-MIYAURA CROSS-COUPLING REACTION; SYNTHESISED;

LITHIUM;

EID: 77949397833     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527210790231937     Document Type: Review

References (95)

1. Zhang, W.X.; Xi, Z. 1-lithio-1,3-dienes as useful building blocks in organic synthesis. Pure Appl. Chem., 2009, 81, 235-246.
2. Fang, H.Y.; Song, Q.L.; Wang, Z.H.; Xi, Z.F. Concise synthesis of stereodefined dienols and cyclopentadienes via direct addition of 1-bromomagnesiobutadienes and 1-lithiobutadienes to carbonyl compounds. Tetrahedron Lett., 2004, 45, 5159-5162.
3. Song, Q.L.; Li, Z.P.; Chen, J,L.; Wang, C.Y.; Xi, Z.F. Acyl-lithiation of olefins: Formation of cyclopentenones from 1-lithio-butadienes and CO. Org. Lett., 2002, 4, 4627-4629.
4. Schlosser, M. The activation of organolithium reagents. J. Organomet. Chem., 1967, 8, 9-16.
5. Venturello, P. Reactivity of α,β-unsaturated acetals with electrophiles in the presence of organolithium potassium reagents. J. Chem. Soc. Chem. Commun., 1992, 1032-1033.
6. Deagostino, A.; Prandi, C.; Zavattaro, C.; Venturello, P. Functionalized 1-alkoxy-1,3-dienes: Their preparation and applications in synthetic organic. Eur. J. Org. Chem., 2006, 2463-2483.
7. Deagostino, A.; Prandi, C.; Venturello, P. α,β-unsaturated acetals in synthesis. Curr. Org. Chem., 2003, 7, 821-839.
8. Blangetti, M.; Deagostino, A.; Prandi, C.; Zavattaro, C.; Venturello, P. N-Metalated imines by reaction of 1,1-diethoxybut-2-ene with aromatic nitriles, as useful intermediates for the synthesis of substituted pyrimidines and cyclopentenones. Chem. Commun., 2008, 14, 1689-1691.
9. Feuerstein, M.; Chahen, L.; Doucet, H.; Santelli, M. Efficient synthesis of enynes by tetraphosphine-palladium-catalysed reaction of vinyl bromides with terminal alkynes. Tetrahedron, 2006, 62, 112-120.
10. Fang, X.N.; Jiang, M.H.; Hu, R.H.; Cai, M.Z. Facile Stereoselective Synthesis of (E)-1-Arylseleno-Substituted 1,3-Enynes and Their Applications in Synthesis of (E)-Enediynes. Synth. Commun., 2008, 38, 4170-4181.
11. Gu, X.X.; Xie, M.H.; Zhao, X.Y.; Sun, Y.; Zhang, W.; Xie, F.D.; Wang, S.W. An efficient synthesis of polysubstituted 1,3-enynes from (E)-β-iodovinyl sulfones and terminal alkynes. Chin. J. Chem., 2008, 26, 1625-1629.
12. Chen, J.J.; Liu, Y.H. Dialkyltitanium-mediated titanation of conjugated 1,3-butadiynes and its coupling reactions with aldehydes: a facile synthesis of stereodefined enynes and trans-enynols. Tetrahedron Lett., 2008, 49, 6655-6658.
13. Liu, Y.; Nishiura, M.; Wang, Y.; Hou, Z.M. pi-Conjugated aromatic enynes as a single-emitting component for white electroluminescence.J. Am. Chem. Soc., 2006, 128, 5592-5593.
14. Zhang, W.X.; Nishiura, M.; Hou, Z.M. Synthesis of (Z)-1-Aza-1,3-enynes by the Cross-Coupling of Terminal Alkynes with Isocyanides Catalyzed by Rare-Earth Metal Complexes. Angew. Chem. Int. Ed. Engl., 2008, 47, 9700-9703.
15. Lu, J.M.; Shi, M. LDA-mediated selective addition reaction of vinylidenecy-clopropanes with aldehydes, ketones, and enones: Facile synthesis of vinylcyclopropenes, allenols, and 1,3-enynes. Org. Lett., 2008, 10, 1943-1946.
16. Watanabe, M.; Nakamura, M.; Satoh, T. Reaction of magnesium alkylidene carbenoids with lithium acetylides and lithium thiolates: a novel synthesis of conjugated enynes and vinyl sulfides. Tetrahedron, 2005, 61, 4409-4418.
17. Blangetti, M.; Deagostino, A.; Rosso, H.; Prandi, C.; Zavattaro, C.; Venturello, P. Rapid and easy access to (E)-1,3-enynes, 1,3-diynes and allenes starting from propargylic acetals, exploiting the different reactivity of lithium and mixed lithium-potassium organometallic reagents. Eur. J. Org. Chem., 2007, 5867-5874.
18. Chen, C.W.; Luh, T.Y. Elimination of β-Thioalkoxy Alcohols under Mitsunobu Conditions. A New Synthesis of Conjugated Enynes from Propargylic Dithioacetals. J. Org. Chem., 2008, 73, 8357-8363.
19. Miller, K.M.; Colby, E.A.; Woodin, K.S.; Jamison, T.F. Asymmetric catalytic reductive coupling of 1,3-enynes and aromatic aldehydes. Adv. Synth. Catal., 2005, 347, 1533-1536.
20. Komanduri, V.; Krische, M.J. Enantioselective reductive coupling of 1,3-enynes to heterocyclic aromatic aldehydes and ketones via rhodiumcatalyzed asymmetric hydrogenation: Mechanistic insight into the role of Bronsted acid additives. J. Am. Chem. Soc., 2006, 128, 16448-16449.
21. Zhao, Y.L.; Chen, L.; Liu, Q.; Li, D.W. Stereoselective C-C bond-forming reaction of α-ethynyl ketene-S,S-acetals with aldehydes in the presence of titanium tetrahalides. Synlett, 2007, 1, 37-42.
22. Luken, C.; Moberg, C. Silaborations of 1,3-enynes - Substrate controlled allene/1,3-diene selectively. Org. Letts., 2008, 10, 2505-2508.
23. Ma, S.M.; He, Q.W.; Jin, X. Tunable 1,3-lithium shift of propargylic/allenylic lithiums formed by conjugate addition of 4-aryl-3-butyn-1-enes with organolithiums and the subsequent transmetalation/Pd(O)- catalyzed coupling reaction with aryl halides. Synlett, 2005, 3, 514-516.
24. Waser, J.; Gonzalez-Gomez, J.C.; Nambu, H.; Huber, P.; Carreira, E.M. Cobalt-catalyzed hydrohydrazination of dienes and enynes: Access to allylic and propargylic hydrazides. Org. Lett., 2005, 7, 4249-4252.
25. Deagostino, A.; Farina, V.; Prandi, C.; Zavattaro, C.; Venturello, P. New metal-catalyzed synthesis of quinoline and chromene skeletons. Eur. J. Org. Chem., 2006, 15, 3451-3456.
26. Bolos, J.; Loscertales, T.; Nieto, J.; Sacristan, A.; Ortiz, J. A. A new efficient synthesis of 3-(hydroxymethyl)-4H-chromen-4-ones. J. Heterocycl. Chem., 2000, 37, 1203-1208.
27. Gunduz, C.; Salan, U.; Ozkul, N.; Basaran, I.; Cakir, U.; Bulut, M. The synthesis and complexation study of some novel 3-methoxyphenyl chromenone crown ethers using conductometry. Dyes Pigm., 2006, 71, 161-167.
28. Murr, M.D.E.; Cano, C.; Golding, B.T.; Hardcastle, I.R.; Hummersome, M.; Frigerio, M.; Curtin, N.J.; Menear, K.; Richardson, C.; Smith, G.C.M.; Griffin, R.J. 8-biarylchromen-4-one inhibitors of the DNA-dependent protein kinase (DNA-PK). Bioorg. Med. Chem. Lett., 2008, 18, 4885-4890.
29. Rueping, M.; Merino, E.; Sugiono, E. Enantioselective organocatalytic reactions of 4-hydroxycoumarin and 4-hydroxypyrone with α,α-unsaturated aldehydes - An efficient Michael addition-acetalization cascade to chromenones, quinolinones and pyranones. Adv. Synth. Catal., 2008, 350, 2127-2131.
30. Marull, M.; Schlosser, M. Selective and efficient structural elaboration of 2-(trifluoromethyl)quinolinones. Eur. J. Org. Chem., 2003, 8, 1576-1588.
31. Lefebvre, O.; Marull, M.; Schlosser, M. 4-(trifluoromethyl)quinoline derivatives. Eur. J. Org. Chem., 2003, 11, 2115-2121.
32. Hessian, K.O.; Flynn, B.L. Iodine-induced reaction cascades for the rapid construction of variously substituted benzothiophenes. Org. Lett., 2003, 5, 4377-4380.
33. Yue, D.; Larock, R.C. Synthesis of 2,3-disubstituted benzo[b]thiophenes via palladium-catalyzed coupling and electrophilic cyclization of terminal acetylenes. J. Org. Chem., 2002, 67, 1905-1909.
34. Flynn, B.L.; Verdier-Pinard, P.; Hamel, E. A novel palladium-mediated coupling approach to 2,3-disubstituted benzo[b]thiophenes and its application to the synthesis of tubulin binding agents. Org. Lett., 2001, 3, 651-654.
35. Hessian, K.O.; Flynn, B.L. Selective endo and exo iodocyclizations in the synthesis of Quinolines and Indoles. Org. Lett., 2006, 8, 243-246.
36. Nadaraj, V.; Selvi, S.T.; Sasi, R. Microwave-assisted synthesis of quinoline alkaloids: 4-Methoxy-1-methyl-2-quinolinone and its analogs. Arkivoc, 2006, 82-89.
37. Tu, S.J.; Jiang, B.; Zhang, J.Y.; Jia, R.H.; Zhang, Y.; Yao, C.S. Efficient and direct synthesis of poly-substituted indeno[1,2-b]quinolines assisted by p-toluene sulfonic acid using high-temperature water and microwave heating via one-pot, three-component reaction. Org. Biomol. Chem., 2006, 4, 3980-3985.
38. Huang, C.C.; Chang, N.C. New approach to 2-quinolinones. Org. Lett., 2008, 10, 673-676.
39. Likhar, P.R.; Subhas, M.S.; Roy, S.; Kantam, M.L.; Sridhar, B.; Seth, R.K.; Biswas, S. Synthesis of highly substituted 2-perfluoroalkyl quinolines by electrophilic iodocyclization of perfluoroalkyl propargyl imines/amines. Org. Biomol. Chem., 2009, 7, 85-93.
40. Mamane, V.; Louerat, F.; Lehl, J.; Abboud, M.; Fort, Y. A general and efficient method for the synthesis of benzo-(iso)quinoline derivatives. Tetrahedron, 2008, 64, 10699-10705.
41. Gai, X.J.; Grigg, R.; Ramzan, M.I.; Sridharan, V.; Collard, S.; Muir, J.E. Pyrazole and benzothiazole palladacycles: stable and efficient catalysts for carbon-carbon bond formation. Chem. Commun., 2000, 20, 2053-2054.
42. Grigg, R.; Koppen, I.; Rasparini, M.; Sridharan, V. Synthesis of spiro- and fused heterocycles by palladium catalysed carbo- and heteroannulation cascades of allenes. Chem. Commun., 2001, 11, 964-965.
43. Brown, S.; Grigg, R.; Hinsley, J.; Korn, S.; Sridharan, V.; Uttley, M. D. Three-component Heck-Diels-Alder cascade processes involving alkylallenes, aryl iodides and dienophiles. Tetrahedron, 2001, 57, 10347-10355.
44. Grigg, R.; Martin, W.; Morris, J.; Sridharan, V. Four-component Pd-catalysed cascade/ring closing metathesis. Synthesis of heterocyclic enones. Tetrahedron, 2005, 61, 11380-11392.
45. Knoke, M.; de Meijere, A. Cyclopropyl building blocks in organic synthesis, part 85. A versatile access to 1-cyclopropyl-2-aryl-1,3,5-hexatrienes - Domino Heck-Diels-Alder reactions of 1,3-dicyclopropyl-1,2-propadiene. Synlett, 2003, 2, 195-198.
46. Inamoto, K.; Yamamoto, A.; Ohsawa, K.; Hiroya, K.; Sakamoto, T. Highly regioselective palladium-catalyzed annulation reactions of heteroatom-substituted allenes for synthesis of condensed heterocycles. Chem. Pharm. Bull., 2005, 53, 1502-1507.
47. Lu, G.L.; Malinakova, H.C. Regio- and diastereoselective insertion of allenes into stable oxapalladacycles with a metal-bonded stereogenic carbon. Preparation of contiguously substituted 3,4-dihydro-2H-1-benzopyrans. J. Org. Chem., 2004, 69, 8266-8279.
48. Fu, C.L.; Ma, S.M. Observation of the first Heck-type cross-coupling reaction of allenes with aryl halides. Synthesis of polysubstituted 1,2-allenyl sulfones. Org. Lett., 2005, 7, 1605-1607.
49. Jiang, X.F.; Ma, X.J.; Zheng, Z.L.; Ma, S. Controllable Cyclization Reactions of 2-(2 ',3 '-Allenyl)acetylacetates Catalyzed by Gold and Palladium Affording Substituted Cyclopentene and 4,5-Dihydrofuran Derivatives with Distinct Selectivity. Chem. Eur. J., 2008, 14, 8572-8578.
50. Deagostino, A.; Prandi, C.; Toppino, A.; Venturello, P. Palladium-catalysed Heck reaction on 1,2-dien-1-ols: a stereoselective synthesis of α-arylated α,β-unsaturated aldehydes. Tetrahedron, 2008, 64, 10344-10349.
51. Deagostino, A.; Prandi, C.; Venturello, P. Palladium-catalyzed Heck reaction on 1-alkoxy-1,3-dienes: A regioselective γ-arylation of α,β-unsaturated carbonyl compounds. Org. Lett., 2003, 5, 3815-3817.
52. Beccaria, L.; Deagostino, A.; Prandi, C.; Zavattaro, C.; Venturello, P. Heck Reaction on 1-Alkoxy-1,3-dienes in Ionic Liquids: A Superior Medium for the Regioselective Arylation of the Conjugated Dienic System. Synlett, 2006, 18, 2989-2992.
53. 4-Chlorodiene)tricarbonyliron Complexes. Organometallics, 2007, 26, 223-229.
54. Wang, Y.; Burton, D.J. Base-catalyzed cyclization of monofluorodienynes: a new route to substituted fluorobenzene derivatives. Tetrahedron Lett., 2006, 47, 9279-9281.
55. Tang, C.J.; Wu, Y.K. On the synthesis of cepacin A. Tetrahedron, 2007, 63, 4887-4906.
56. Denmark, S. E.; Tymonko, S. A. Sequential Cross-Coupling of 1,4-Bissilylbutadienes: Synthesis of Unsymmetrical 1,4-Disubstituted 1,3-Butadienes. J. Am. Chem. Soc., 2005, 127, 8004-8005.
57. Huang, T.H.; Chang, H.M.; Wu, M.Y.; Cheng, C.H. Palladium-catalyzed three-component assembling of allenes, organic halides, and arylboronic acids. J. Org. Chem., 2002, 67, 99-105.
58. Ma, S.M.; Jiao, N.; Ye, L.W. Palladium-catalyzed highly regio- and stereoselective addition of organoboronic acids to allenes in the presence of AcOH. Chem. Eur. J., 2003, 9, 6049-6056.
59. Zhu, G.G.; Zhang, Z.G. Palladium-catalyzed tandem cyclization/suzuki coupling reaction of 1, 2,7-trienes. Org. Lett., 2004, 6, 4041-4044.
60. Tonogaki, K.; Itami, K.; Yoshida, J. Catalytic four-component assembly based on allenylboronate platform: New access to privileged allylic amine structures. J. Am. Chem. Soc., 2006, 128, 1464-1465.
61. Woodward, A.R.; Burks, H.E.; Chan, L.M.; Morken, J. P. Concatenated catalytic asymmetric allene diboration/allylation/functionalization. Org. Lett., 2005, 7, 5505-5507.
62. Balma Tivola, P.; Deagostino, A.; Prandi, C.; Venturello, P. A new synthesis of butadienyl- and styrylboronic esters: highly reactive intermediates for Suzuki cross-coupling. Org. Lett., 2002, 4, 1275-1277.
63. Deagostino, A.; Migliardi, M.; Occhiato, E. G.; Prandi, C.; Zavattaro, C.; Venturello, P. LIC-KOR promoted formation of conjugated dienes as useful building blocks for palladium-catalyzed syntheses. Tetrahedron, 2005, 61, 3429-3436.
64. Shimizu, M.; Kurahashi, T.; Shimono, K.; Tanaka, K.; Nagao, I.; Kiyomoto, S.; Hiyama, T. Facile Synthesis and Palladium-Catalyzed Cross-Coupling Reactions of 2,3-Bis(pinacolatoboryl)-1,3-butadiene. Chem. Asian J., 2007, 2, 1400-1408.
65. Shimizu, M.; Shimono, K.; Schelper, M.; Hiyama, T. Stereoselective Cross-coupling Reaction of 2,4-Diaryl-1,1-diboryl-1,3-butadienes: Stereocontrolled Approach to 1,3,4,6-Tetraarylated 1,3,5-Hexatrienes. Synlett, 2007, 12, 1969-1971.
66. Kurahashi, T.; Hata, T.; Masai, H.; Kitagawa, H.; Shimizu, M.; Hiyama, T. Geminal dimetalation of alkylidene-type carbenoids with silylboranes and diborons. Tetrahedron, 2002, 58, 6381-6395.
67. Hata, T.; Kitagawa, H.; Masai, H.; Kurahashi, T.; Shimizu, M.; Hiyama, T. Geminal Difunctionalization of Alkenylidene-Type Carbenoids by Using Interelement Compounds. Angew. Chem., Int. Ed. Engl., 2001, 40, 790-792.
68. Babudri, F.; Farinola, G.M.; Naso, F.; Ragni, R.; Spina, G. A Novel Stereo-selective Synthesis of Symmetrical (1E,3E)-1,4-Diarylbuta-1,3-dienes. Synthesis, 2007, 19, 3088-3092.
69. Morita, R.; Shirakawa, E.; Tsuchimoto, T.; Kawakami, Y. Synthesis of multisubstituted 1,3-butadienes using the ruthenium-catalysed double addition of trimethylsilyldiazomethane to alkynylboronates. Org. Biomol. Chem., 2005, 3, 1263-1268.
70. Lopez, S.; Montenegro, J.; Saa, C. Highly Convergent, Stereospecific Synthesis of 11-cis-Retinoids by Metal-Catalyzed Cross-Coupling Reactions of (Z)-1-Alkenylmetals. J. Org. Chem. 2007, 72, 9572-9581.
71. Ohmura, T.; Yamamoto, Y.; Miyaura, N. Rhodium-or Iridium-Catalyzed trans-Hydroboration of Terminal Alkynes, Giving (Z)-1-Alkenylboron Compounds. J. Am. Chem. Soc., 2000, 122, 4990-4991.
72. Uenishi, J.; Beau, J.M.; Armstrong, R.W.; Kishi, Y. Dramatic rate enhancement of Suzuki diene synthesis. Its application to palytoxin synthesis. J. Amer. Chem. Soc., 1987, 109, 4756-4758.
73. Rousset, S.; Abarbri, M.; Thibonnet, J.; Duchene, A.; Parrain, J. L. Palladium-catalysed annulation reaction of allenyltins with β-iodo vinylic acids: selective synthesis of α-pyrones. Chem. Commun., 2000, 20, 1987-1988.
74. Cherry, K.; Duchene, A.; Thibonnet, J.; Parrain, J.L.; Abarbri, M. Regioselective synthesis of 1,4,6-trisubstituted-2-pyridinones and 2,3-disubstituted (2H)-isoquinolin-1-ones via tandem Stille reaction/heterocyclisation. Synthesis, 2005, 14, 2349-2356.
75. Huang, C.W.; Shanmugasundaram, M.; Chang, H.M.; Cheng, C.H. Highly chemoselective coupling of allenylstannanes with organic iodides promoted by Pd(PPh3)(4)/LiCl: an efficient method for the synthesis of substituted allenes. Tetrahedron, 2003, 59, 3635-3641.
76. Lavecchia, G.; Berteina-Raboin, S.; Guillaumet, G. Selective bifunctionalization of pyrido[2,3-d]pyrimidines in positions 2 and 4 by SNAr and palladium-catalyzed coupling reactions. Tetrahedron Lett., 2005, 46, 5851-5855.
77. Mukai, C.; Takahashi, Y. A new entry to the synthesis of 2,3-disubstituted indoles. Org. Lett., 2005, 7, 5793-5796.
78. Hodgson, D.M.; Chung, Y.K.; Nuzzo, I.; Freixas, G.; Kulikiewicz, K. K.; Cleator, E.; Paris, J. M. Intramolecular cyclopropanation of unsaturated terminal epoxides and chlorohydrins. J. Am. Chem. Soc. 2007, 129, 4456-4462.
79. Trostyanskaya, I.G.; Maslova, E.N.; Kazankova, M.A.; Beletskaya, I.P. Transition metal-catalyzed cross-coupling of 1,4-diiodobutadienes with thiols-A novel route to 1,4-bis(R-sulfanyl)buta-1,3-dienes. Russ. J. Org. Chem., 2008, 44, 24-30.
80. Ogasawara, M.; Okada, A.; Watanabe, S.; Fan, L.; Uetake, K.; Nakajima, K.; Takahashi, T. Synthesis, Structure, and Reactivity of (1,2,3-η3-Butadien-3-yl)palladium Complexes. Organometallics, 2007, 26, 5025-5029.
81. Barluenga, J.; Aznar, F.; Moriel, P.; Valdés, C. Palladium-Catalyzed Amination of 1-Bromo-and 1-Chloro-1,3-butadienes: A General Method for the Synthesis of 1-Amino-1,3-butadienes. Adv. Synth. Catal., 2004, 346, 1697-1701.
82. Shi, Y.; Ramgren, S.D.; Blum, S.A. Palladium-Catalyzed Carboauration of Alkynes and Palladium/Gold Cross-Coupling. Organometallics, 2009, 28, 1275-1277.
83. Leitner, A.; Larsen, J.; Steffens, C.; Hartwig, J.F. Palladium-Catalyzed Addition of Mono-and Dicarbonyl Compounds to Conjugated Dienes. J. Org. Chem. 2004, 69, 7552-7557.
84. Gulias, M.; Duran, J.; Lopez, F.; Castedo, L.; Mascarenas, J.L. Palladium-Catalyzed[4 + 3] Intramolecular Cycloaddition of Alkylidenecyclopropanes and Dienes. J. Am. Chem. Soc., 2007, 129, 11026-11027.
85. Chang, K.J.; Rayabarapu, D.K.; Yang, F.Y.; Cheng, C.H. Unusual palladium-catalyzed silaboration of allenes using organic iodides as initiators: Mechanism and application. J. Am. Chem. Soc., 2005, 127, 126-131.
86. Ohmura, T.; Taniguchi, H.; Suginome, M. J. Palladium-catalyzed asymmetric silaboration of allenes. Am. Chem. Soc., 2006, 128, 13682-13683.
87. Hong, Y.T.; Yoon, S.K.; Kang, S.K.; Yu, C.M. A stereoselective carbocyclization of bis(allenes) with germylstannane catalyzed by palladium complexes. Eur. J. Org. Chem., 2004, 22, 4628-4635.
88. Toyofuku, M.; Murase, E.; Fujiwara, S.; Shin-ike, T.; Kuniyasu, H.; Kambe, N. Palladium-catalyzed selenoacylation of allenes leading to the regioselective formation of functionalized allyl selenides. Org. Lett., 2008, 10, 3957-3960.
89. Patil, N.T.; Pahadi, N.K.; Yamamoto, Y. An improved catalytic system, Pd(PPh3)4/PhCOOH combined catalyst, for the allylation of carbon pronucleophiles with allenes. Synthesis, 2004, 13, 2186-2190.
90. Trost, B.M.; Simas, A.B.C.; Plietker, B.; Jakel, C.; Xie, J. Enantioselective palladium-catalyzed addition of 1,3-dicarbonyl compounds to an allene derivative. Chem. Eur. J., 2005, 11, 7075-7082.
91. Alcaide, B.; Almendros, P.; del Campo, T.M. Reaction of two different α-allenols in a heterocyclization/cross-coupling sequence: Convenient access to functionalized buta-1,3-dienyl dihydrofurans. Angew Chem., Int. Ed. Engl., 2006, 45, 4501-4504.
92. Ma, S.M.; Yu, F.; Gao, W.Z. Studies on Pd(II)-catalyzed coupling-cyclization of α-or β-amino allenes with allylic halides. J. Org. Chem., 2003, 68, 5943-5949.
93. Chengebroyen, J.; Linke, M.; Robitzer, M.; Sirlin, C.; Pfeffer, M. Palladium-mediated intramolecular C-N bond formation involving allyl substituted pyridines. Application to a novel strategy for the synthesis of the skeleton of berberinium derivatives. J. Organomet. Chem., 2003, 687, 313-321.
94. Franzen, J.; Lofstedt, J.; Dorange, I.; Bäckvall, J. E. Allenes as carbon nucleophiles in palladium-catalyzed reactions: Observation of anti attack of allenes on (π-allyl)palladium complexes. J. Am. Chem. Soc., 2002, 124, 11246-11247.
95. Hershberger, J.C.; Zhang, L.; Lu, G.L.; Malinakova, H.C. Polymer-supported palladacycles: Efficient reagents for synthesis of Benzopyrans with palladium recovery. Relationship among resin loading, Pd: P ratio, and reactivity of immobilized palladacycles. J. Org. Chem., 2006, 71, 231-235.